80390-90-5Relevant articles and documents
Anodic Oxidation of 3-Amino-5-(pyrid-4-yl)-1,2-dihydropyrid-2-one (Amrinone)
Hagen, V.,Klauschenz, E.,Pragst, F.
, p. 793 - 803 (2007/10/02)
The anodic behavior of the cardiotonic drug 3-amino-5-(pyrid-4-yl)-1,2-dihydropyrid-2-one 1 and of 6 compounds with similar structure was investigated at platinum and vitreous carbon electrodes in acetonitrile and in aqueous medium.Caused by the 3-amino group 1 is oxidized at a relatively small oxidation potential in an irreversible two-electron process.Depending on the addition of a strong base or a strong acid the oxidation potential vs.SCE in acetonitrile is -0.08 V (anion), +0.66 V (neutral compound), +0.93 V (monocation) or +1.15 V (dication).In H2O a strong decrease of the oxidation potential with increasing pH was found as a reason for the sensitivity of 1 against oxygen in alkaline solution.The anodic oxidation of 3-dimethylamino-5-(pyrid-4-yl)-1,2-dihydro-pyrid-2-one 3 in 0.1m H2SO4 leads to 5-(pyrid-4-yl)-piperidine-2,3,6-trione 9a or 5-(pyrid-4-yl)-piperidine-2,3,4-trione 9b, which is also the oxidation product of 1 at small concentration.At high concentration of 1 coupling reactions at the 3-amino-group lead to dimeric products, which could not be identified.